EP0442360A1 - Procédé de transfert de colorants azoiques - Google Patents

Procédé de transfert de colorants azoiques Download PDF

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Publication number
EP0442360A1
EP0442360A1 EP91101564A EP91101564A EP0442360A1 EP 0442360 A1 EP0442360 A1 EP 0442360A1 EP 91101564 A EP91101564 A EP 91101564A EP 91101564 A EP91101564 A EP 91101564A EP 0442360 A1 EP0442360 A1 EP 0442360A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
radical
alkoxy
hydrogen
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP91101564A
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German (de)
English (en)
Other versions
EP0442360B1 (fr
Inventor
Karl-Heinz Dr. Etzbach
Ruediger Dr. Sens
Matthias Dr. Wiesenfeldt
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BASF SE
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BASF SE
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Publication date
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Publication of EP0442360A1 publication Critical patent/EP0442360A1/fr
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Publication of EP0442360B1 publication Critical patent/EP0442360B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • B41M5/388—Azo dyes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/913—Material designed to be responsive to temperature, light, moisture
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/914—Transfer or decalcomania

Definitions

  • the present invention relates to a new process for transferring azo dyes, which have a thiophene-based diazo component, from a support to a plastic-coated paper using an energy source.
  • a transfer sheet containing a thermally transferable dye in one or more binders, optionally together with suitable auxiliaries is supported on a support with an energy source, e.g. with a heating head, heated by short heating impulses (duration: fractions of a second) from the back, whereby the dye migrates from the transfer sheet and diffuses into the surface coating of a recording medium.
  • an energy source e.g. with a heating head
  • short heating impulses duration: fractions of a second
  • EP-A-216 483 or EP-A-258 856 describes azo dyes which have diazo components based on thiophene and coupling components based on aniline.
  • disazo dyes based on thiophene and aniline are known from EP-A-218 937 for this purpose.
  • EP-A-302 682 teaches the thermal transfer of azo dyes which are derived from 2-aminothiophenes which have a condensed carbonyl group in ring position 5.
  • the object of the present invention was to provide a method for transferring azo dyes, the dyes being intended to meet the above-mentioned requirements as well as possible.
  • Residues Y in formula I are e.g. Ethylene, 1,2- or 1,3-propylene, 1,2-, 1,3-, 1,4- or 2,3-butylene, pentamethylene, hexamethylene or 2-methylpentamethylene.
  • Suitable radicals R1, R2, R3, R4, R5 and R7 in formula I are e.g. Methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
  • R1 and R4 are furthermore, for example pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl or isodecyl.
  • Residues R1 are, for example, undecyl, dodecyl, tridecyl, isotridecyl (the names isooctyl, isononyl, isodecyl and isotridecyl are trivial names and come from the alcohols obtained after oxosynthesis - see also Ullmann's Encyclopedia of Industrial Chemistry, 4th edition, volume 7 , Pages 215 to 217 and volume 11, pages 435 and 436) tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, benzyl, 1- or 2-phenylethyl, 3-hydroxybutyl, 3-hydroxyheptyl, 10-hydroxy-1-ethyldecyl, 2-cyanoethyl, 3-cyanopropyl, 3-cyano-2-methylpentyl, 7-cyanononyl, 7
  • R4 and R5 are also, for example methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy or sec-butoxy.
  • Residues R4 are still e.g. Pentyloxy, isopentyloxy, neopentyloxy, hexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, nonyloxy or decyloxy.
  • Residues R5 are still e.g. Methylthio, ethylthio, propylthio, isopropylthio or butylthio.
  • the dyes of the formula I are known from EP-A-201 896 or can be obtained by the methods mentioned there.
  • the dyes transferred in the process according to the invention are generally distinguished by improved migration properties in the recording medium at room temperature, easier thermal transferability, higher photochemical stability, easier technical accessibility, better resistance to moisture and chemical substances, higher color strength , better solubility, higher color purity and higher thermal stability.
  • the dyes are in a suitable organic solvent, for example chlorobenzene, isobutanol, methyl ethyl ketone, methylene chloride, toluene, tetrahydrofuran or mixtures thereof, processed with one or more binders, optionally with the addition of auxiliaries, to form a printing ink.
  • a suitable organic solvent for example chlorobenzene, isobutanol, methyl ethyl ketone, methylene chloride, toluene, tetrahydrofuran or mixtures thereof.
  • binders optionally with the addition of auxiliaries
  • binders All resins or polymer materials which are soluble in organic solvents and are capable of binding the dye to the inert support in an abrasion-resistant manner are suitable as binders. Preference is given to binders which, after the printing ink has dried in air, absorb the dye in the form of a clear, transparent film without the dye crystallizing out visibly.
  • binders are cellulose derivatives, e.g. Methyl cellulose, ethyl cellulose, ethyl hydroxyethyl cellulose, hydroxypropyl cellulose, cellulose acetate or cellulose acetobutyrate, starch, alginates, alkyd resin, vinyl resin, polyvinyl alcohol, polyvinyl acetate, polyvinyl butyrate or polyvinyl pyrrolidone.
  • cellulose derivatives e.g. Methyl cellulose, ethyl cellulose, ethyl hydroxyethyl cellulose, hydroxypropyl cellulose, cellulose acetate or cellulose acetobutyrate, starch, alginates, alkyd resin, vinyl resin, polyvinyl alcohol, polyvinyl acetate, polyvinyl butyrate or polyvinyl pyrrolidone.
  • Polymers and copolymers of acrylates or their derivatives such as polyacrylic acid, polymethyl methacrylate or styrene-acrylate copolymers, polyester resins, polyamide resins, polyurethane resins or natural CH resins, such as gum arabic, are also suitable as binders.
  • Other suitable binders are e.g. in DE-A-3 524 519.
  • Preferred binders are ethyl cellulose, ethyl hydroxyethyl cellulose or polyvinyl butyrate.
  • the ratio of binder to dye preferably varies between 5: 1 and 1: 1.
  • auxiliaries such as are specified in EP-A-227 092, EP-A-192 435 or the patent applications cited therein, are also suitable as auxiliaries, in addition, in particular, organic additives which cause the transfer dyes to crystallize out during storage and when the ink ribbon is heated prevent, e.g. Chlolesterol or vanillin.
  • Inert carriers are e.g. Tissue, blotting or glassine paper or plastic films with good heat resistance, e.g. optionally metal-coated polyester, polyamide or polyimide.
  • the inert carrier is optionally additionally coated with a slip layer on the side facing the thermal head in order to prevent the thermal head from sticking to the carrier material.
  • Suitable lubricants are described, for example, in EP-A-216 483 or EP-A-227 095.
  • the thickness of the dye carrier is generally 3 to 30 microns, preferably 5 to 10 microns.
  • all temperature-stable plastic layers with an affinity for the dyes to be transferred whose glass transition temperature should be below 150 ° C, e.g. modified polycarbonates or polyester.
  • Suitable formulations for the receiver layer composition are e.g. in EP-A-227 094, EP-A-133 012, EP-A-133 011, EP-A-111 004, JP-A-199 997/1986, JP-A-283 595/1986, JP- A-237 694/1986 or JP-A-127 392/1986 described in detail.
  • the transmission takes place by means of an energy source, e.g. by means of a laser or by means of a thermal head which must be able to be heated to a temperature of ⁇ 300 ° C. so that the dye transfer can take place in the time range t: 0 ⁇ t ⁇ 15 msec.
  • the dye migrates from the transfer sheet and diffuses into the surface coating of the recording medium.

Landscapes

  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
EP91101564A 1990-02-15 1991-02-06 Procédé de transfert de colorants azoiques Expired - Lifetime EP0442360B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4004600 1990-02-15
DE4004600A DE4004600A1 (de) 1990-02-15 1990-02-15 Verfahren zur uebertragung von azofarbstoffen

Publications (2)

Publication Number Publication Date
EP0442360A1 true EP0442360A1 (fr) 1991-08-21
EP0442360B1 EP0442360B1 (fr) 1995-11-22

Family

ID=6400157

Family Applications (1)

Application Number Title Priority Date Filing Date
EP91101564A Expired - Lifetime EP0442360B1 (fr) 1990-02-15 1991-02-06 Procédé de transfert de colorants azoiques

Country Status (4)

Country Link
US (1) US5145828A (fr)
EP (1) EP0442360B1 (fr)
JP (1) JPH05584A (fr)
DE (2) DE4004600A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0578870A1 (fr) * 1992-07-14 1994-01-19 Agfa-Gevaert N.V. Colorants thiazolylazoanilines pour utilisation dans le transfert thermique de colorants par sublimation
EP0581342A1 (fr) * 1992-07-14 1994-02-02 Agfa-Gevaert N.V. Elément donneur de colorant pour le transfert thermique de colorants par sublimation
US5432040A (en) * 1992-07-14 1995-07-11 Agfa-Gevaert, N.V. Dye-donor element for use according to thermal dye sublimation transfer
EP0665117A1 (fr) * 1994-01-31 1995-08-02 Agfa-Gevaert N.V. Image produite par transfert thermique de colorant, ayant une stabilité à la lumière améliorée
WO1996030214A1 (fr) * 1995-03-25 1996-10-03 Imperial Chemical Industries Plc Impression par transfert thermique a diffusion de colorants
CN109574880A (zh) * 2017-09-29 2019-04-05 华东理工大学 一种荧光探针及其制备方法和用途

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5571765A (en) * 1994-01-31 1996-11-05 Agfa-Gevaert N.V. Thermal dye transfer image with improved light-fastness
JP5829648B2 (ja) 2013-06-11 2015-12-09 株式会社中部コーポレーション 食材カッター

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0216483A1 (fr) * 1985-08-27 1987-04-01 Zeneca Limited Impression par transfert thermique
EP0235939A2 (fr) * 1986-02-28 1987-09-09 Zeneca Limited Impression par transfert thermique
EP0258856A2 (fr) * 1986-09-05 1988-03-09 BASF Aktiengesellschaft Méthode de transfert de colorant
EP0344592A2 (fr) * 1988-05-31 1989-12-06 BASF Aktiengesellschaft Procédé de transfert de colorants azoiques
EP0352006A2 (fr) * 1988-07-20 1990-01-24 Imperial Chemical Industries Plc L'impression par transfert thermique

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0216483A1 (fr) * 1985-08-27 1987-04-01 Zeneca Limited Impression par transfert thermique
EP0235939A2 (fr) * 1986-02-28 1987-09-09 Zeneca Limited Impression par transfert thermique
EP0258856A2 (fr) * 1986-09-05 1988-03-09 BASF Aktiengesellschaft Méthode de transfert de colorant
EP0344592A2 (fr) * 1988-05-31 1989-12-06 BASF Aktiengesellschaft Procédé de transfert de colorants azoiques
EP0352006A2 (fr) * 1988-07-20 1990-01-24 Imperial Chemical Industries Plc L'impression par transfert thermique

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0578870A1 (fr) * 1992-07-14 1994-01-19 Agfa-Gevaert N.V. Colorants thiazolylazoanilines pour utilisation dans le transfert thermique de colorants par sublimation
EP0581342A1 (fr) * 1992-07-14 1994-02-02 Agfa-Gevaert N.V. Elément donneur de colorant pour le transfert thermique de colorants par sublimation
US5432040A (en) * 1992-07-14 1995-07-11 Agfa-Gevaert, N.V. Dye-donor element for use according to thermal dye sublimation transfer
EP0665117A1 (fr) * 1994-01-31 1995-08-02 Agfa-Gevaert N.V. Image produite par transfert thermique de colorant, ayant une stabilité à la lumière améliorée
WO1996030214A1 (fr) * 1995-03-25 1996-10-03 Imperial Chemical Industries Plc Impression par transfert thermique a diffusion de colorants
US6057264A (en) * 1995-03-25 2000-05-02 Imperial Chemical Industries Plc Dye diffusion thermal transfer printing
CN109574880A (zh) * 2017-09-29 2019-04-05 华东理工大学 一种荧光探针及其制备方法和用途

Also Published As

Publication number Publication date
DE59106925D1 (de) 1996-01-04
EP0442360B1 (fr) 1995-11-22
JPH05584A (ja) 1993-01-08
US5145828A (en) 1992-09-08
DE4004600A1 (de) 1991-08-22

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